JPS58185562A - １，４−ジヒドロピリジン誘導体 - Google Patents
１，４−ジヒドロピリジン誘導体Info
- Publication number
- JPS58185562A JPS58185562A JP57067759A JP6775982A JPS58185562A JP S58185562 A JPS58185562 A JP S58185562A JP 57067759 A JP57067759 A JP 57067759A JP 6775982 A JP6775982 A JP 6775982A JP S58185562 A JPS58185562 A JP S58185562A
- Authority
- JP
- Japan
- Prior art keywords
- ester
- acid
- nidoradoethyl
- group
- nitrophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 150000002148 esters Chemical class 0.000 abstract description 65
- 150000001875 compounds Chemical class 0.000 abstract description 17
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
- -1 ethyl diester Chemical class 0.000 abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
- 210000004351 coronary vessel Anatomy 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 206010020772 Hypertension Diseases 0.000 abstract description 2
- 210000001627 cerebral artery Anatomy 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002324 hematogenic effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 40
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 30
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 30
- 238000010898 silica gel chromatography Methods 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000003814 drug Substances 0.000 description 9
- 229910004679 ONO2 Inorganic materials 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000017531 blood circulation Effects 0.000 description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- RMZQSAMHIQBMLW-UHFFFAOYSA-N 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1[N+]([O-])=O RMZQSAMHIQBMLW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 210000001367 artery Anatomy 0.000 description 6
- 230000004087 circulation Effects 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000005457 ice water Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 101150041968 CDC13 gene Proteins 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 description 4
- 229910001961 silver nitrate Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YPMPTULBFPFSEQ-PLNGDYQASA-N ethyl (z)-3-aminobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)N YPMPTULBFPFSEQ-PLNGDYQASA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- APTMRLLOXPDHNL-UHFFFAOYSA-N 2-bromoethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCBr APTMRLLOXPDHNL-UHFFFAOYSA-N 0.000 description 2
- PZISUEUDMNMOCP-UHFFFAOYSA-N 2-chloropropyl 3-oxobutanoate Chemical compound CC(Cl)COC(=O)CC(C)=O PZISUEUDMNMOCP-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000001105 femoral artery Anatomy 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- 210000002385 vertebral artery Anatomy 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- PAWSVPVNIXFKOS-IHWYPQMZSA-N (Z)-2-aminobutenoic acid Chemical compound C\C=C(/N)C(O)=O PAWSVPVNIXFKOS-IHWYPQMZSA-N 0.000 description 1
- UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TZDPJNSHSWMCPN-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 TZDPJNSHSWMCPN-UHFFFAOYSA-N 0.000 description 1
- ZHLDJBAROHNALN-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-2,4-dihydro-1H-pyridine-3,3-dicarboxylic acid Chemical compound CC1NC(=CC(C1(C(=O)O)C(=O)O)C1=CC(=CC=C1)[N+](=O)[O-])C ZHLDJBAROHNALN-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- XJOLYWNYMOPRKQ-WAYWQWQTSA-N 2-methoxyethyl (z)-3-aminobut-2-enoate Chemical compound COCCOC(=O)\C=C(\C)N XJOLYWNYMOPRKQ-WAYWQWQTSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- PBJZBRWKTBIWOK-FPLPWBNLSA-N 2-propoxyethyl (z)-3-aminobut-2-enoate Chemical compound CCCOCCOC(=O)\C=C(\C)N PBJZBRWKTBIWOK-FPLPWBNLSA-N 0.000 description 1
- KMOIUTFJKPNORM-UHFFFAOYSA-N 3-bromopropyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCBr KMOIUTFJKPNORM-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- MOFSXCCLSWSZDJ-VURMDHGXSA-N CC(C)CCOC(=O)/C=C(/C)\N Chemical compound CC(C)CCOC(=O)/C=C(/C)\N MOFSXCCLSWSZDJ-VURMDHGXSA-N 0.000 description 1
- 101100433727 Caenorhabditis elegans got-1.2 gene Proteins 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- LLVIIIKNSZRDTA-UHFFFAOYSA-N bis(2-nitroethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound [O-][N+](=O)CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC[N+]([O-])=O)C1C1=CC=CC([N+]([O-])=O)=C1 LLVIIIKNSZRDTA-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004982 dihaloalkyl group Chemical group 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YCKAGGHNUHZKCL-XQRVVYSFSA-N propan-2-yl (z)-3-aminobut-2-enoate Chemical compound CC(C)OC(=O)\C=C(\C)N YCKAGGHNUHZKCL-XQRVVYSFSA-N 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57067759A JPS58185562A (ja) | 1982-04-22 | 1982-04-22 | １，４−ジヒドロピリジン誘導体 |
| EP83302075A EP0092936B1 (de) | 1982-04-22 | 1983-04-13 | 1,4-Dihydropyridinderivate |
| DE8383302075T DE3370620D1 (en) | 1982-04-22 | 1983-04-13 | 1,4-dihydropyridine derivatives |
| US06/486,508 US4472411A (en) | 1982-04-22 | 1983-04-19 | 1,4-Dihydropyridine derivatives and use as vasodilators |
| SE8305467A SE440648B (sv) | 1982-04-22 | 1983-10-05 | 1,4-dihydropyridin-dikarboxylsyra-nitratoalkylestrar |
| AU19941/83A AU565424B2 (en) | 1982-04-22 | 1983-10-06 | 2,6-dimethyl-4 (nitrophenyl) -1,4-dihydropyridine-3,5 -dicarboxylic acid esters |
| BE0/211728A BE898024A (fr) | 1982-04-22 | 1983-10-19 | Derives de 1,4-dihydropyridine et compositions pharmaceutiques a action vasodilatatrice les contenant. |
| NL8303616A NL8303616A (nl) | 1982-04-22 | 1983-10-20 | 1,4-dihydropyridinederivaten. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57067759A JPS58185562A (ja) | 1982-04-22 | 1982-04-22 | １，４−ジヒドロピリジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58185562A true JPS58185562A (ja) | 1983-10-29 |
| JPS635024B2 JPS635024B2 (de) | 1988-02-01 |
Family
ID=13354183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57067759A Granted JPS58185562A (ja) | 1982-04-22 | 1982-04-22 | １，４−ジヒドロピリジン誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4472411A (de) |
| EP (1) | EP0092936B1 (de) |
| JP (1) | JPS58185562A (de) |
| AU (1) | AU565424B2 (de) |
| BE (1) | BE898024A (de) |
| DE (1) | DE3370620D1 (de) |
| NL (1) | NL8303616A (de) |
| SE (1) | SE440648B (de) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59110671A (ja) * | 1982-11-30 | 1984-06-26 | バイエル・アクチエンゲゼルシヤフト | １，４−ジヒドロピリジン誘導体 |
| EP0207674A2 (de) | 1985-06-14 | 1987-01-07 | Sankyo Company Limited | 1,4-Dihydropyridinderivate, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung |
| JPS62292757A (ja) * | 1986-06-12 | 1987-12-19 | Taisho Pharmaceut Co Ltd | １，４−ジヒドロピリジン誘導体 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0127150A3 (de) * | 1983-05-27 | 1987-07-22 | Fujisawa Pharmaceutical Co., Ltd. | 2,6-Disubstituierte-1,4-dihydropyridin-Derivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
| GB8314744D0 (en) * | 1983-05-27 | 1983-07-06 | Fujisawa Pharmaceutical Co | 2 6-disubstituted-1 4-dihydropyridine derivative |
| JPS60156671A (ja) * | 1984-01-25 | 1985-08-16 | Yamanouchi Pharmaceut Co Ltd | ジヒドロピリジン誘導体およびその製造法 |
| US4730052A (en) * | 1984-07-13 | 1988-03-08 | Taisho Pharmaceutical Co., Ltd. | Method for preparing unsymmetrical 1,4-dihydropyridine-3,5-dicarboxylic acid diesters |
| JPS62174050A (ja) * | 1985-10-21 | 1987-07-30 | Nippon Shoji Kk | ３−アミノカルボニル−１，４−ジヒドロピリジン−５−カルボン酸誘導体、その製法および医薬組成物 |
| US4780538A (en) * | 1986-02-12 | 1988-10-25 | Merck & Co., Inc. | Process for 1,4-dihydropyridine compounds using a titanamine catalyst |
| JPS6396126A (ja) * | 1986-10-13 | 1988-04-27 | Taisho Pharmaceut Co Ltd | 安定化組成物 |
| US5047543A (en) * | 1988-11-24 | 1991-09-10 | Taisho Pharmaceutical Co., Ltd. | 1,4-dihydropyridine derivatives |
| NL9001752A (nl) * | 1990-08-02 | 1992-03-02 | Cedona Pharm Bv | Nieuwe 1,4-dihydropyridinederivaten. |
| DE60234057D1 (de) | 2001-07-25 | 2009-11-26 | Raptor Pharmaceutical Inc | Zusammensetzungen und verfahren zur modulation des transports durch die blut-hirn-schranke |
| EP1889198B1 (de) | 2005-04-28 | 2014-11-26 | Proteus Digital Health, Inc. | Pharma-informatiksystem |
| WO2008036682A2 (en) | 2006-09-18 | 2008-03-27 | Raptor Pharmaceutical Inc. | Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates |
| DK3395372T3 (da) | 2009-02-20 | 2022-04-19 | Enhanx Biopharm Inc | System til afgivelse af glutathion-baseret medikament |
| EP2427178B1 (de) | 2009-05-06 | 2023-01-04 | Laboratory Skin Care, Inc. | Dermale freisetzungszusammensetzung mit wirkstoff-calciumphosphat-partikelkomplexen und anwendungsverfahren |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670827C3 (de) * | 1967-03-20 | 1974-10-24 | Bayer Ag, 5090 Leverkusen | 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin |
| DE2117573C3 (de) * | 1971-04-10 | 1978-07-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von unsymmetrischen l,4-Dihydropyridin-3,5dicarbonsäureestern, sowie ihre Verwendung als Arzneimittel |
| DE2847236A1 (de) * | 1978-10-31 | 1980-05-14 | Bayer Ag | Neue dihydropyridine mit substituierten estergruppierungen, mehrer verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1982
- 1982-04-22 JP JP57067759A patent/JPS58185562A/ja active Granted
-
1983
- 1983-04-13 DE DE8383302075T patent/DE3370620D1/de not_active Expired
- 1983-04-13 EP EP83302075A patent/EP0092936B1/de not_active Expired
- 1983-04-19 US US06/486,508 patent/US4472411A/en not_active Expired - Fee Related
- 1983-10-05 SE SE8305467A patent/SE440648B/sv not_active IP Right Cessation
- 1983-10-06 AU AU19941/83A patent/AU565424B2/en not_active Ceased
- 1983-10-19 BE BE0/211728A patent/BE898024A/fr not_active IP Right Cessation
- 1983-10-20 NL NL8303616A patent/NL8303616A/nl not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59110671A (ja) * | 1982-11-30 | 1984-06-26 | バイエル・アクチエンゲゼルシヤフト | １，４−ジヒドロピリジン誘導体 |
| EP0207674A2 (de) | 1985-06-14 | 1987-01-07 | Sankyo Company Limited | 1,4-Dihydropyridinderivate, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung |
| JPS62292757A (ja) * | 1986-06-12 | 1987-12-19 | Taisho Pharmaceut Co Ltd | １，４−ジヒドロピリジン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3370620D1 (en) | 1987-05-07 |
| SE8305467D0 (sv) | 1983-10-05 |
| JPS635024B2 (de) | 1988-02-01 |
| SE8305467L (sv) | 1985-04-06 |
| EP0092936B1 (de) | 1987-04-01 |
| EP0092936A1 (de) | 1983-11-02 |
| US4472411A (en) | 1984-09-18 |
| BE898024A (fr) | 1984-04-19 |
| SE440648B (sv) | 1985-08-12 |
| AU565424B2 (en) | 1987-09-17 |
| AU1994183A (en) | 1985-04-18 |
| NL8303616A (nl) | 1985-05-17 |
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